diff --git a/pkgs/development/python-modules/debugpy/default.nix b/pkgs/development/python-modules/debugpy/default.nix
index d9b3dfce72a5..0a75e20aa0a9 100644
--- a/pkgs/development/python-modules/debugpy/default.nix
+++ b/pkgs/development/python-modules/debugpy/default.nix
@@ -13,16 +13,18 @@
   pytest-timeout,
   importlib-metadata,
   psutil,
+  untangle,
   django,
-  requests,
+  flask,
   gevent,
   numpy,
-  flask,
+  requests,
+  typing-extensions,
 }:
 
 buildPythonPackage rec {
   pname = "debugpy";
-  version = "1.8.8";
+  version = "1.8.9";
   format = "setuptools";
 
   disabled = pythonOlder "3.8";
@@ -31,7 +33,7 @@ buildPythonPackage rec {
     owner = "microsoft";
     repo = "debugpy";
     rev = "refs/tags/v${version}";
-    hash = "sha256-zkNV+tFRAxTdl+lCPD4XYI1Oz0dVyX4GGuNdfzy2sJU=";
+    hash = "sha256-JgYGdCGzzktigjEKMPbkcSJlFPYSEFEJvmIFfR0qSZM=";
   };
 
   patches =
@@ -104,6 +106,7 @@ buildPythonPackage rec {
     ## Used by test helpers:
     importlib-metadata
     psutil
+    untangle
 
     ## Used in Python code that is run/debugged by the tests:
     django
@@ -111,6 +114,7 @@ buildPythonPackage rec {
     gevent
     numpy
     requests
+    typing-extensions
   ];
 
   preCheck =
diff --git a/pkgs/development/python-modules/debugpy/hardcode-gdb.patch b/pkgs/development/python-modules/debugpy/hardcode-gdb.patch
index d977f78771f5..422690870154 100644
--- a/pkgs/development/python-modules/debugpy/hardcode-gdb.patch
+++ b/pkgs/development/python-modules/debugpy/hardcode-gdb.patch
@@ -1,5 +1,5 @@
 diff --git a/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py b/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py
-index a1a852a0..0bb91807 100644
+index 2e328f61..ba7221fe 100644
 --- a/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py
 +++ b/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py
 @@ -412,7 +412,7 @@ def run_python_code_linux(pid, python_code, connect_debugger_tracing=False, show
diff --git a/pkgs/development/python-modules/debugpy/hardcode-lldb.patch b/pkgs/development/python-modules/debugpy/hardcode-lldb.patch
index 5edbe3545695..07c5ff8c7d03 100644
--- a/pkgs/development/python-modules/debugpy/hardcode-lldb.patch
+++ b/pkgs/development/python-modules/debugpy/hardcode-lldb.patch
@@ -1,5 +1,5 @@
 diff --git a/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py b/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py
-index 0bb91807..8026a5ad 100644
+index ba7221fe..24efc1ed 100644
 --- a/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py
 +++ b/src/debugpy/_vendored/pydevd/pydevd_attach_to_process/add_code_to_python_process.py
 @@ -503,7 +503,7 @@ def run_python_code_mac(pid, python_code, connect_debugger_tracing=False, show_d
diff --git a/pkgs/development/python-modules/debugpy/hardcode-version.patch b/pkgs/development/python-modules/debugpy/hardcode-version.patch
index 9fa42a0605f8..00e77bd75b94 100644
--- a/pkgs/development/python-modules/debugpy/hardcode-version.patch
+++ b/pkgs/development/python-modules/debugpy/hardcode-version.patch
@@ -1,5 +1,5 @@
 diff --git a/setup.py b/setup.py
-index 1bfba237..414bb4d5 100644
+index d16a27c5..a7e407e1 100644
 --- a/setup.py
 +++ b/setup.py
 @@ -12,7 +12,6 @@ import sys
@@ -27,7 +27,7 @@ index 1bfba237..414bb4d5 100644
          long_description=long_description,
          long_description_content_type="text/markdown",
 diff --git a/src/debugpy/public_api.py b/src/debugpy/public_api.py
-index 9d0f705a..ee0b26ca 100644
+index c61a2607..f26f8272 100644
 --- a/src/debugpy/public_api.py
 +++ b/src/debugpy/public_api.py
 @@ -7,8 +7,6 @@ from __future__ import annotations
@@ -39,7 +39,7 @@ index 9d0f705a..ee0b26ca 100644
  
  # Expose debugpy.server API from subpackage, but do not actually import it unless
  # and until a member is invoked - we don't want the server package loaded in the
-@@ -191,4 +189,4 @@ def trace_this_thread(__should_trace: bool):
+@@ -192,4 +190,4 @@ def trace_this_thread(__should_trace: bool):
      """
  
  
diff --git a/pkgs/development/python-modules/debugpy/skip-attach-pid-tests.patch b/pkgs/development/python-modules/debugpy/skip-attach-pid-tests.patch
index cef0a97eb300..af3362990dd9 100644
--- a/pkgs/development/python-modules/debugpy/skip-attach-pid-tests.patch
+++ b/pkgs/development/python-modules/debugpy/skip-attach-pid-tests.patch
@@ -1,5 +1,5 @@
 diff --git a/tests/debug/runners.py b/tests/debug/runners.py
-index dc60d0ae..cf4a06a3 100644
+index cac4fbf5..079bb743 100644
 --- a/tests/debug/runners.py
 +++ b/tests/debug/runners.py
 @@ -163,7 +163,7 @@ def _attach_common_config(session, target, cwd):
@@ -12,10 +12,10 @@ index dc60d0ae..cf4a06a3 100644
  
      log.info("Attaching {0} to {1} by PID.", session, target)
 diff --git a/tests/debugpy/test_attach.py b/tests/debugpy/test_attach.py
-index 017d7f59..63e86328 100644
+index 78453bfe..458716af 100644
 --- a/tests/debugpy/test_attach.py
 +++ b/tests/debugpy/test_attach.py
-@@ -151,8 +151,7 @@ def test_reattach(pyfile, target, run):
+@@ -153,8 +153,7 @@ def test_reattach(pyfile, target, run):
  
  
  @pytest.mark.parametrize("pid_type", ["int", "str"])
@@ -24,4 +24,4 @@ index 017d7f59..63e86328 100644
 +@pytest.mark.skip(
      reason="https://github.com/microsoft/debugpy/issues/311",
  )
- def test_attach_pid_client(pyfile, target, pid_type):
+ @pytest.mark.flaky(retries=2, delay=1)